o-Fluoro-beta-nitrostyrene → Benzyl 3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-ylcarbamate

HRID 2361257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361257
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:3]=[CH:2]1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1/[CH:28]=[CH:29]/[N+:30]([O-:32])=[O:31]>ClCCl>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH:28]([C:3]1[C:4]2[C:9](=[CH:8][C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH2:29][N+:30]([O-:32])=[O:31]

Komponenten

4

Edukt 2

HCID 5383481o-Fluoro-beta-nitrostyreneHCID 67994742Benzyl 1H-indol-6-ylcarbamate

Produkt 1

HCID 67994648Benzyl 3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-ylcarbamateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

Benzyl 1H-indol-6-ylcarbamate (0.981 g, 3.68 mmol) and (E)-1-fluoro-2-(2-nitrovinyl)benzene (0.770 g, 4.60 mmol) were suspended and well mixed in dichloromethane (15 mL). The suspension was concentrated under vacuum to dryness. The solid mixture was then heated at 105° C. under nitrogen for 7 hr. The mixture was subjected to ISCO (120 g silica gel, solid loading, 20-45% ethyl acetate) to afford the desired product (1.287 g, 2.97 mmol, 81% yield) as a white solid.

Aufarbeitung

  1. concentrationThe suspension was concentrated under vacuum to dryness

Quellen und Nachweise

ORD-Eintrag
ord-da96014e59594580abfe3d40e9bb1bf8
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685969B2

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